AI Operations Specialist, Trilogy (Remote) - $200,000/year USD

We are hiring operators capable of constructing and reconstructing systems built for scale.

Operational excellence at Trilogy is not optional—it is the competitive edge that defines us. We move quickly to acquire software companies and scale them even more rapidly. To sustain this pace, we require leaders who architect lean, automated systems rather than expand complexity through headcount.

You will take full ownership of end-to-end transformations spanning our global portfolio. This might involve redesigning the offboarding process for 1,200+ employees following an acquisition, replacing platforms like Jira and Salesforce with AI agents, or creating automations that remove thousands of manual hours. Execution will be rapid, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks that keep you focused on results.

Trilogy manages a portfolio of 100+ products with relentless efficiency. We function with reduced hierarchy, accelerated cycles, and elevated standards compared to conventional enterprise settings. This is an opportunity to generate large-scale impact without navigating bureaucracy or overseeing inflated teams.

We do not maintain steady-state operations. We do not delegate transformation to others. And we do not bring on individuals who require approval or extensive teams to execute. We seek a select group of deeply technical, execution-oriented leaders who treat automation as leverage and velocity as a strategic advantage. If this describes you—this environment will suit you well.

What You Will Be Doing

• Driving high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions
• Building and deploying automations that replace CRM and task management platforms using Python and LLM APIs
• Implementing AI-powered workflows through Cursor, Windsurf, and MCP to remove manual processes and cut latency
• Owning initiatives from assessment through deployment, applying proven playbooks and executive-level decision-making
• Passing a hands-on technical assessment that validates your capability to design and implement AI-first solutions
  
  

What You Won’t Be Doing

• Building or managing large teams or depending on organizational layers to achieve outcomes
• Spending time in prolonged alignment sessions or waiting for consensus before acting
• Handing off the complex work to IT departments or third-party vendors—you will architect and deliver the solution directly
• Running steady-state operations—this position centers on transformation and speed
  
  

AI Operations Specialist Key Responsibilities

Architect and implement AI-first operational systems that remove manual workload, reduce complexity, and enable scalable execution across Trilogy's global software portfolio.

Basic Requirements

• Located in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
• 5+ years of operational leadership in enterprise software
• 3+ years in customer-facing roles (Support, Sales, Collections, etc.)
• Proven ability to write automation in Python and integrate with LLM APIs
• Experience using Cursor, Windsurf, MCP, or similar tools to deliver production-grade automations
• Demonstrated capacity to act quickly, think independently, and deliver high-stakes outcomes without oversight
  
  

Nice-to-have Requirements

• Background leading large-scale organizational transitions such as M&A integrations or mass offboarding
• Track record of designing and deploying AI-driven operational systems
• Portfolio of automations you have personally built and deployed at scale
  
  

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5145-PK-Lahore-AIOperationsSp